Senior Director of Product Management

Senior Director of Product ManagementReports to: CEO

About Us:  

At BenchPrep, we are committed to revolutionizing learning by delivering the most advanced and flexible learning experience for certification, credentialing, test prep, continuing education, and training. Our learning platform helps associations, credentialing bodies and training companies deliver a highly engaging and effective learning experience for individuals looking to advance their careers. We incorporate the latest in learner-centered technology, including personalization, gamification, data science, usability and omni-channel delivery.  The number of learners using our cloud-based learning platform has grown significantly, reaching nearly 12 million humans around the world in 2024, a testament to the success and impact of our innovative learning solutions.

Role OverviewBenchPrep is hiring an execution-first product leader to translate strategy into a clear, prioritized, and delivery-ready roadmap, lead and develop a team, drive predictable, on-time delivery in partnership with Engineering, and ensure launches lead to real adoption, commercial impact, and measurable outcomes.

This leader will establish strong planning and decision-making cadences, foster clarity and alignment across cross-functional stakeholders, and build a team culture rooted in accountability, customer focus, and follow-through.

This role is ideal for someone who is hands-on and rigorous and thrives on consistently shipping high-quality product while maintaining a sharp focus on outcomes such as adoption and revenue impact. 

What you'll do in the role:

• Own and evolve BenchPrep’s platform-level product strategy, translating company goals into a clear, prioritized roadmap with measurable outcomes.
• Lead, coach, and develop a high-performing product management team, setting clear expectations, operating rhythms, and accountability standards.
• Partner closely with Engineering to drive predictable, high-quality delivery, balancing speed, quality, and technical rigor.
• Collaborate with Sales and Customer Success on pipeline strategy, deal support, and expansion opportunities, ensuring product decisions drive revenue impact.
• Serve as a key cross-functional leader, aligning Product, Engineering, Product Marketing, Sales, and Customer Success on priorities, tradeoffs, and sequencing.
• Represent Product externally in customer and prospect conversations, roadmap webinars, and strategic deal solutioning.
• Build and maintain a strong product analytics discipline, using data to inform prioritization, diagnose performance, and drive action.

What you can expect:

• A highly hands-on leadership role with meaningful ownership over product strategy, execution, and outcomes.
• Close partnership with executive leadership to shape BenchPrep’s future platform investments.
• A collaborative, low-ego environment that values clarity, thoughtful debate, and bias toward action.
• The opportunity to influence how millions of learners experience digital education worldwide.

How you’ll become successful: 

• Establish clear planning, prioritization, and decision-making cadences that improve roadmap predictability and delivery confidence.
• Drive adoption and measurable impact for paid and strategic product capabilities.
• Translate customer and market insights into focused platform investments without losing execution momentum.
• Build trust across teams by communicating product direction, rationale, and tradeoffs with clarity and consistency.
• Develop a product organization known for accountability, customer focus, and shipping quality work.

Skills & Experiences We Value:

• 10+ years of experience in Product Management leadership within B2B SaaS environments.
• Proven success translating strategy into execution while driving revenue, adoption, and customer value.
• Strong operational discipline in roadmap planning, delivery, and cross-functional execution.
• Experience partnering with Sales, Customer Success, and Product Marketing on GTM strategy and deal support.
• Excellent communication, prioritization, analytical, and decision-making skills.
• Low-ego, high-ownership leadership style with a strong bar for product quality.
• Bonus experience in EdTech, learning platforms, assessment, credentialing, or multi-tenant enterprise SaaS.
• Experience building or maturing a product analytics function from the ground up is a plus.

Travel Requirements: Willingness to travel to customer locations and company retreats as needed (approximately 3-5 per year).

At BenchPrep, we value our differences, and we encourage all to apply—especially those whose identities are traditionally underrepresented in tech. Research shows that candidates from underrepresented backgrounds often don't apply for roles if they don't meet all the criteria.  We strongly encourage you to apply if you’re interested and even if you don’t meet 100% of the listed requirements.  We’d be excited to see how you can boast our team with your unique experience.  

Life at BenchPrep:

We work at BenchPrep because we’re dedicated to the mission and each day we have an opportunity to be challenged and learn. We work hard and have lots of fun. Culture is our lifeline at BenchPrep. We celebrate our people, both professionally and personally. We care about learning so much that we offer employees annual stipend dollars to develop their skills so they can continue to operate everyday with new skills. It’s no wonder we’ve been selected so often on various Best Places to Work lists!

Flexibility: 

We’re a remote-first company that empowers our team to work where they thrive. We hire talent from across the U.S., embracing the flexibility and inclusivity that remote work offers. Our interviews, onboarding, and daily collaboration happen virtually, with intentional moments for connection.

While remote work is our foundation, we also believe in the value of in-person collaboration. That’s why we host “Together Weeks” each year in Chicago — three days of learning, innovation, and celebration with the entire team. These gatherings help strengthen relationships and fuel creativity while maintaining the flexibility of remote work year-round.

Comp & Benefits: 

This role offers flexibility in terms of experience and expertise. Throughout the interview process, we’ll evaluate your background to determine where you align within our compensation range.The salary range for this position is between $190,000 - $210,000, and is set based on Chicago market data.  Please note this refers to the amount BenchPrep is willing to pay at the time of this posting. 

• Medical insurance covering 80% of premiums for you and your dependents.
• Dental, Vision, Short & Long Term Disability, Life Insurance and other Voluntary benefits.
• 401(K) Safe Harbor Non-Elective 3% Contribution
• Flex PTO (our version of unlimited PTO), Wellness Days, Birthday PTO, Winter Break + a generous company holiday calendar
• Annual Learning Stipend of $1,200
• Parental Leave 
• $500 towards workstation setup upon hire, and a monthly stipend for other expenses after that
• … and the list goes on! 

We are an equal opportunity employer and value diversity at our company. We do not discriminate on the basis of race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, or disability status.  Please note, we are unable to accept applications from candidates outside of the US at this time.

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